74044-75-0

Upstream product

• 63700-05-0 1,2;5,6-dianhydro-3,4-O-isopropylidene-D-mannitol 
• 53754-41-9 1,6-di-O-(p-toluenesulfonyl)-3,4-O-isopropylidene-D-mannitol 
• 60-29-7 diethyl ether 
• 3969-84-4 3,4-di-O-isopropylidene-D-mannitol 
• 69-65-8 mannitol 
• 3969-59-3 mannitol triacetonide 
• 172657-94-2 O³,O⁴-isopropylidene-1,6-diiodo-1,6-dideoxy-D-mannitol 

Downstream Products

• 159716-56-0 C₂₀H₂₂O₆ 
• 171524-74-6 1,6-dideoxy-D-mannitol 2,5-di-p-toluenesulfonate 
• 248244-34-0 1,2-bis[(2S,3S,4S,5S)-3,4-dihydroxyl-2,5-dimethylphospholanyl]benzene 
• 259535-67-6 (3aS,4S,6S,6aS)-tetrahydro-2,2,4,6-tetramethyl-5-phenyl-4H-phospholo[3,4-d]-1,3-dioxole 
• 259752-00-6 (2S,3S,4S,5S)-3,4-dihydroxy-2,5-dimethyl-1-phenylphospholane 
• 159716-54-8 (2R,3R,4R,5R)-2,5-dibenzoyloxy-3,4-O-(1-methylethylidene)-3,4-hexanediol 
• 74044-76-1 1,6-dideoxy-3,4-O-isopropylidene-D-mannitol 2,5-di-p-toluenesulfonate 

Relevant academic research and scientific papers

An efficient, one-pot synthesis of fosfomycin dialkyl esters from (R)-2-tosyloxypropanal

(R)-2-Tosyloxypropanal (4) was prepared from D-mannitol in a 7-step sequence (51% overall yield). Addition of dialkyl phosphonates to 4 in the presence of titanium isopropoxide and the subsequent treatment with DBU stereoselectively afforded, in one-pot, fosfomycin dimethyl (5a) and dibenzyl (5b) esters both in 58% isolated yield.

Asymmetric catalysis based on chiral phospholanes and hydroxyl phospholanes

Chiral phosphine ligands derived from chiral natural products including D-mannitol and tartaric acid. The ligands contain one or more 5-membered phospholane rings with multiple chiral centers, and provide high stereoselectivity in asymmetric reactions.

A Novel Chiral Ferrocenyl Phosphine Ligand from Sugar: Applications in Rh-Catalyzed Asymmetric Hydrogenation Reactions

(Matrix Presented) A new chiral ferrocenyl diphosphine ligand 3 was synthesized from readily available D-mannitol. Rh-complex with this ligand showed high enantioselectivity and reactivity in the asymmetric hydrogenation of dehydroamino acid derivatives and itaconic acid derivatives. Up to over 99% ee and 10 000 TON were achieved with this catalytic system.

Asymmetric catalysis based on chiral phospholanes and hydroxyl phospholanes

Chiral phosphine ligands derived from chiral natural products including D-mannitol and tartaric acid. The ligands contain one or more 5-membered phospholane rings with multiple chiral centers, and provide high stereoselectivity in asymmetric reactions.

Synthesis of chiral hydroxyl phospholanes from D-mannitol and their use in asymmetric catalytic reactions

Chiral hydroxyl monophosphane 3 [(2S,3S,4S,5S)-3,4-dihydroxy-2,5-dimethyl-1-phenylphospholane] and bisphospholanes 5a [1,2-bis[(2S,3S,4S,5S)-3,4-dihydroxy-2,5-dimethylphospholanyl]benzene] and 5b [1,2-bis[(2S,3S,4S,5S)-2,5-diethyl-3,4-dihydroxyphospholanyl]benzene] were synthesized from readily available D-mannitol in high yields. Strategies for protection and deprotection of OH-groups in the presence of phosphines have been explored. Rate acceleration in the Baylis - Hillman reaction was observed when a hydroxyl phosphine was used as the catalyst. Rhodium complexes with chiral bisphospholanes are highly enantioselective catalysts for the asymmetric hydrogenation of various kinds of functionalized olefins such as dehydroamino acid derivatives, itaconic acid derivatives, and enamides. An interesting feature of the hydroxyl phospholane system is that hydrogenation of some substrates can be carried out in water with >99% ee and 100% conversion (e.g., itaconic acid).

Highly Flexible Synthetic Routes to Functionalized Phospholanes from Carbohydrates

Highly functionalized phospholanes 15, 17, and 26 and the corresponding diastereomers in which the configurations of the phospholane carbon-2 and carbon-5 are inverted can be readily prepared from D-mannitol by displacement of the appropriate dimesylate or cyclic sulfate with dilithium-phosphide reagents. The diols from which these ligands are prepared can also be converted into diarylphosphinite ligands. A route to related monophosphines bearing hemilabile tert-butylthio groups is also described. Complexes of these ligands and of related deprotected derivatives are potentially useful for enantioselective catalysis in organic and aqueous media.

Rhodium-hydroxyl bisphospholane catalyzed highly enantioselective hydrogenation of dehydroamino acids and esters

A chiral hydroxyl bisphospholane, 1,2-bis[(2S,3S,4S,5S)-3,4-dihydroxyl-2,5-dimethylphospholanyl]benzene (4), was synthesized from readily available D-mannitol. Its Rh(I) complex catalyzes asymmetric hydrogenation of dehydroamino acids and their ester derivatives with excellent enantioselectivities (98 to >99% ee).

A practical synthesis of (R)- and (S)-(E)-4-hydroxyalk-2-enals, cytotoxic products of the microsomal lipid peroxidation

The chemical synthesis of some (S)- and (R)-(E)-4-hydroxyalk-2-enals, important products of lipid peroxidation (LPO), has been carried out via enantiomerically pure 2-benzoyloxyaldehydes, chiral key intermediates obtained from two diastereomeric diepoxide

A convergent synthesis of optically active aspyrone

Aspyrone (1) was elaborated in an optically pure form by the key reaction involving a nucleophilic addition of δ-lactone enolate to 2-tosyloxyaldehyde and a subsequent in situ formation of epoxide.